DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Election/Restrictions
Claim 1 is allowable. Claims 10-14, previously withdrawn from consideration as a result of a restriction requirement, require all the limitations of an allowable claim. Pursuant to the procedures set forth in MPEP § 821.04(a), the restriction requirement between inventions of product and process for preparing the product, as set forth in the Office action mailed on 26 November 2025, is hereby withdrawn and claims 10-14 are hereby rejoined and fully examined for patentability under 37 CFR 1.104. In view of the withdrawal of the restriction requirement, applicant(s) are advised that if any claim presented in a divisional application is anticipated by, or includes all the limitations of, a claim that is allowable in the present application, such claim may be subject to provisional statutory and/or nonstatutory double patenting rejections over the claims of the instant application. Once the restriction requirement is withdrawn, the provisions of 35 U.S.C. 121 are no longer applicable. See In re Ziegler, 443 F.2d 1211, 1215, 170 USPQ 129, 131-32 (CCPA 1971). See also MPEP § 804.01.
Claims 1-14, submitted on 16 June 2026, represent all claims currently under consideration.
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
Response to Arguments
The 35 U.S.C. § 112(b) rejection of Claim 4 is withdrawn. Applicant has amended Claim 4 to remove the phrase “at least one selected from the group consisting of”, obviating the indefiniteness issue.
The 35 U.S.C. § 103 rejection of Claims 1-9 over Kim in view of Mitsubishi and Martyanov is withdrawn. Applicant has amended the claims to recite only aluminum and magnesium as the metal alkoxide catalysts. Neither Kim nor Mitsubishi teach, suggest, or provide motivation for the use of aluminum or magnesium as the metal alkoxide catalyst. Martyanov discloses the use of a magnesium catalyst for the transesterification of an ester and an alcohol for the production of biofuel. Applicant argues that both the objective and mechanism of Martyanov are entirely different from the process of the examined application, and that none of the distinctive features nor advantageous effects of the use of the specific metal alkoxide catalysts of the examined application would have been derived or predicted from Martyanov. The Examiner finds these arguments to be persuasive. Applicant shows that the use of catalysts other than magnesium or aluminum results in higher levels of methanol and more metal impurities present in the final product. The data presented by Martyanov shows that magnesium alkoxides react much more slowly than calcium alkoxides, and the reaction is deactivated after approximately four hours. Thus, the artisan would not be motivated to select magnesium for this reaction, and would not expect the advantageous effects demonstrated in the examined application.
The 35 U.S.C. § 103 rejection of Claims 1-9 over Gan in view of Mitsubishi and Martyanov is withdrawn for the reasons described above.
Response to Amendment
As a result of the amendments to Claim 1, which eliminated all metal alkoxides except for those containing aluminum or magnesium, Claim 5 is rejected under 35 U.S.C. § 112(d) and 35 U.S.C. § 112(b) as Claim 5 claims the metal alkoxide calcium methoxide. Newly amended Claim 1 does not state that the catalyst can be a calcium alkoxide, causing this claim to be broader than Claim 1. There is also a lack of antecedent basis for the use of calcium methoxide as Claim 1 does not provide the basis for calcium alkoxides as the catalyst.
Claim Objections
Claim 7 is objected to because of the following informalities: There is an erroneous period after the clause “at a temperature of 70°C”. Appropriate correction is required.
Claims 5 and 12 are objected to because of the following informalities: The claims reference compounds “aluminum isoprepoxide”, and magnesium isoprepoxide”. The Examiner is assuming these should read “isopropoxide”. Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)- NEW GROUNDS OF REJECTION
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 5 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Claim 5 recites the limitation "calcium methoxide" in line 5. There is insufficient antecedent basis for this limitation in the claim as the use of calcium alkoxides as the catalyst is not established in Claim 1, which Claim 5 depends upon.
Claim 11 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Claim 11 is indefinite because it is unclear from the definition of X (at least one selected from the group consisting of…) if the compounds of Chemical Formula I can have more than one metal as part of the formula, i.e. if a compound of Chemical Formula I can be (Ni-Fe)(O-R)a, or other complexes with more than one metal.
Claims 10-14 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Claim 10 is indefinite because of the limitation of “metal alkoxide catalyst which includes at least one metal…” (emphasis added). The use of “includes” is indefinite because it is unclear if the limitations following are merely exemplary or are required limitations of the claim. Claims 11-14 are similarly rejected as indefinite for depending upon an indefinite claim without resolving the underlying issue of indefiniteness.
Claim Rejections - 35 USC § 112(d)- NEW GROUNDS OF REJECTION
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 5 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 5 claims “calcium methoxide” as one of the catalysts. Claim 5 depends on Claim 1, which states that only aluminum or magnesium alkoxides can be used as catalysts in this reaction, causing Claim 5 to be broader than Claim 1. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 103- NEW GROUNDS OF REJECTION
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 10-14 are rejected under 35 U.S.C. 103 as being unpatentable over Kim (KR 20000051813; Publication Date: 16 August 2000) in view of Mitsubishi Chemical Corp (JP H0959224; Publication Date: 4 March 1997) and Martyanov (Applied Catalysis A: General, 339, 1, 2008, 45-52).
Determining the Scope and Contents of the Prior Art:
Kim (See IDS, 17 August 2023) discloses a process for preparing asymmetric linear carbonate esters by transesterification in the presence of a catalyst with two different symmetrical linear carbonate esters, using an alkoxide salt of Group IA element as the reaction catalyst (Claim 1). Claim 2 claims the method of claim 1 wherein the symmetric linear carbonate comprises two different selected from the group consisting of dimethyl carbonate, diethyl carbonate, dipropyl carbonate, and dibutyl carbonate. The amount of catalyst used is 0.0001 to 5% by weight, preferably 0.01 to 1% by weight of catalyst regardless of the kind of reactor used for the reaction (Page 5). No particular limitation is placed on the molar ratio between the two different symmetrical linear carbonic acid esters that are starting materials, and it is preferable to focus on obtaining the maximum yield of the final product asymmetric linear carbonic acid ester. Usually from 10:1 to 1:10, and reacting in different, but equivalent molar ratios depending on the starting materials, are advantageous in terms of productivity (Page 5). Further, the reaction temperature is not particularly limited, but it is preferable to react at a temperature adjacent to the boiling point of the reactant and more preferably 40°-200°C. This is because when the reaction temperature is less than 40°C, the production rate of the final product is slow, and when the temperature exceeds 200°C, decomposition of reactants and production of by products is high, resulting in undesirable properties (Page 5). After the reaction, the reaction mixture is separated from the unreacted symmetrical linear carbonic acid ester by a distillation method such as pressure, atmospheric pressure, or reduced pressure (Page 5). Thus, prior to this purification step, Kim discloses an asymmetric linear carbonate which also includes the metal alkoxide catalyst. Example 1 provides an example where 10 moles of dimethyl carbonate and 10 moles of diethyl carbonate were reacted with LiOCH, and heated to 110°C.
Kim does not disclose the use of the claimed metal alkoxides in the transesterification reaction.
Mitsubishi Chemical Corp (See IDS, 17 August 2023) provides a method for efficiently and industrially producing an alkylaryl carbonate in high purity. The alkylaryl carbonate is separated by distillation from the reaction mixture obtained by the transesterification reaction of the dialkyl carbonate with the diaryl carbonate and the other fractions and distillation residue are recycled to the transesterification reaction system (Abstract). Specific examples of alkyl carbonates include methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, t-butyl, and methylcyclopropyl. Dimethyl carbonate and diethylcarbonate are particularly preferred (Paragraph 0010). In the transesterification reaction of the present invention, the molar ratio of the dialkyl carbonate to the diaryl carbonate is theoretically 1:1, but is not limited thereto and can be used in a wide range, and is usually in the range of 1:20 to 20:1, preferably 3:1 to 1:3. The reaction temperature is usually in the range of 30 to 300°C, preferably 50 to 200°C (Paragraph 0017). Any catalyst may be used as long as it is generally used for transesterification. Examples include inorganic acids, alkoxides of alkyl metals or alkaline earth metals, alkoxides or halides of transition metals such as iron, tin, cobalt, and vanadium, and compounds of molybdenum, bismuth, tellurium, scandium, manganese, and zirconium (Paragraph 0018). Among these catalysts, an alkoxide or halide of a transition metal, and a compound of molybdenum, bismuth, tellurium, scandium, manganese, and zirconium are preferable. The amount of catalysts to be used varies depending on the kind of the catalysts to be used, but is 1-50000 ppm in the reactant solution (Paragraph 0019). It is not always necessary to use a solvent (Paragraph 0020). The target product can be obtained by distillation of the reaction mixture, or after separating the catalyst by filtration, centrifugation, or the like (Paragraph 0021). Thus, Mitsubishi also discloses an asymmetric linear carbonate which comprises a metal alkoxide catalyst prior to this separation.
Martyanov discloses the catalytic activity of calcium methoxides (specifically Ca(OCH3)2) in the transesterification of tributyrine (Abstract).
Ascertaining the Differences Between the Prior Art and the Claims at Issue:
Kim does not disclose the use of the claimed metal alkoxides in the synthesis of the claimed compounds, while Mitsubishi and Martyanov do not disclose the synthesis of the specific claimed compounds but use the claimed catalysts in the synthesis of similar compouds.
Resolving the Level of Ordinary Skill in the Pertinent Art:
The artisan would have training in synthetic chemistry, with a focus in the synthesis of organic compounds using metal catalysts.
Considering Objective Evidence Present in the Application Indicating Obviousness or Nonobviousness:
Kim, Mitsubishi, and Martyanov are considered analogous to the claimed invention as all are involved in performing transesterification reactions. Therefore, it would have been prima facie obvious to one of ordinary skill in the art the time of the effective filing date of the instant application to modify the method of producing asymmetric linear carbonates disclosed by Kim by replacing the catalysts of Kim with the metal alkoxide catalysts of Mitsubishi, such as alkoxides of iron, tin, cobalt, vanadium, or compounds of molybdenum, tellurium scandium, manganese, or zirconium, to arrive at the claimed invention. Martyanov demonstrates that other metal alkoxides, such as calcium dimethoxide, are useful as catalysts in transesterification reactions. The substitution of the catalysts of Kim with the specific metal alkoxides claimed in this invention, as taught by Mitsubishi and Martyanov, is prima facie obvious simple substitution of one known element for another to obtain predictable results (See MPEP § 2143 I (B)); the catalysts claimed in the examined application are known in the art to be useful for similar transesterification reactions, as shown by both Mitsubishi and Martyanov, and the artisan would recognize this, and have a reasonable expectation of success in performing this substitution. Moreover, the selection of the specific metal alkoxide catalysts of Claim 12 is prima facie obvious substitution of an equivalent known for the same purpose (See MPEP § 2144.06 II); Martyanov shows that calcium methoxide is useful in transesterification processes, and thus, it would be obvious to use this catalyst in the claimed transesterification reaction.
Claims 10-14 are rejected under 35 U.S.C. 103 as being unpatentable over Gan (EP 0885874; Publication Date: 23 December 1998) in view of Mitsubishi Chemical Corp (JP H0959224; Publication Date: 4 March 1997) and Martyanov (Applied Catalysis A: General, 339, 1, 2008, 45-52).
Determining the Scope and Contents of the Prior Art:
Gan discloses a method of synthesizing unsymmetric linear organic carbonates comprising the reaction of two symmetric dialkyl carbonates in the presence of a nucleophilic reagent or an electron donating reductant as a catalyst (Abstract). The two symmetric dialkyl carbonates are reacted in the presence of a nucleophilic reagent or electron donating reductant as a catalyst, wherein R1 and R2 can be either saturated or unsaturated alkyl or aryl groups. The two symmetric dialkyl carbonates are preferably present in the starting reaction mixture in a molar ratio of about 9:1 to 1:9
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(Page 3, Lines 15-19). At least two types of catalysts are able to initiate the ester exchange reaction of the present invention, namely, a nucleophilic reagent such as an alkoxide and an amide, an organic or aryl anion and an electron donating reductant inlcuding an alkali metal such as lithium, an alkalated carbon such as lithiated carbon and a samarium salt. Suitable nucleophilic reagents include lithium dialkylamide, lithium alkoxide, an alkyl lithium, and an aryl lithium (Page 3, Lines 38-46). The catalyst is easily separated from the reaction mixture by filtration through a column of alumina or silica gel. After removing the catalyst, the product is readily purified by utilizing commonly known separation techniques such as vacuum distillation, normal pressure distillation, high pressure distillation, extraction, crystallization, chromatography, and the like (Page 3, Lines 54-57). Thus, Gan discloses an asymmetric linear carbonate which comprises a metal alkoxide catalyst prior to this purification step.
Gan does not disclose the use of the claimed metal alkoxides in the transesterification reaction.
The teachings of Mitsubishi and Martyanov are previously described and are fully incorporated into this rejection.
Ascertaining the Differences Between the Prior Art and the Claims at Issue:
Gan does not disclose the use of the claimed metal alkoxides in the transesterification process, while Mitsubishi and Martyanov do not disclose the specific esters.
Resolving the Level of Ordinary Skill in the Pertinent Art:
The artisan would have training in synthetic chemistry, with a focus in the synthesis of organic compounds using metal catalysts.
Considering Objective Evidence Present in the Application Indicating Obviousness or Nonobviousness:
Gan, Mitsubishi, and Martyanov are considered analogous to the claimed invention as all are involved in performing transesterification reactions. Therefore, it would have been prima facie obvious to one of ordinary skill in the art the time of the effective filing date of the instant application to modify the method of producing asymmetric linear carbonates disclosed by Gan by replacing the catalysts of Gan with the metal alkoxide catalysts of Mitsubishi, such as alkoxides of iron, tin, cobalt, vanadium, or compounds of molybdenum, tellurium scandium, manganese, or zirconium, to arrive at the claimed invention. Martyanov demonstrates that other metal alkoxides, such as calcium dimethoxide, are useful as catalysts in transesterification reactions. The substitution of the catalysts of Gan with the specific metal alkoxides claimed in this invention, as taught by Mitsubishi and Martyanov, is prima facie obvious simple substitution of one known element for another to obtain predictable results (See MPEP § 2143 I (B)); the catalysts claimed in the examined application are known in the art to be useful for similar transesterification reactions, as shown by both Mitsubishi and Martyanov, and the artisan would recognize this, and have a reasonable expectation of success in performing this substitution. Moreover, the selection of the specific metal alkoxide catalysts of Claim 12 is prima facie obvious substitution of an equivalent known for the same purpose (See MPEP § 2144.06 II); Martyanov shows that calcium methoxide is useful in transesterification processes, and thus, it would be obvious to use this catalyst in the claimed transesterification reaction.
Allowable Subject Matter
Claims 1-4, 6, and 8-9 are allowed.
Claim 7 is objected to but otherwise allowable.
The following is an examiner’s statement of reasons for allowance: There is no prior art which teaches the synthesis of asymmetric linear alkyl carbonates using aluminum or magnesium alkoxides as the catalyst (See STN Search, Search Notes). The closest prior art comes from Kim and Mitsubishi, cited above. These references teach the use of different metal alkoxide catalysts, with no teaching, suggestion or motivation to utilize aluminum or magnesium. U.S. Patent No. 4,182,726 (Patent Date: 8 January 1980) discloses the synthesis of aromatic carbonates via transesterification utilizing transition metal complexes (Abstract). One catalyst used in these reactions is aluminum isopropoxide (Example 4). However, the reaction only obtained an 11% conversion, with other catalysts such as titanium tetramethoxide showing conversions of over 80% (Example 18). Applicant has further provided data demonstrating that aluminum and magnesium alkoxides unexpectedly result in reduced methanol formation as a by-product compared to other metallic catalysts, as well as improved purity over the metal alkoxide catalysts which have previously been utilized in the art.
Any comments considered necessary by applicant must be submitted no later than the payment of the issue fee and, to avoid processing delays, should preferably accompany the issue fee. Such submissions should be clearly labeled “Comments on Statement of Reasons for Allowance.”
Conclusion
Claims 1-4, 6, and 8-9 are allowed.
Claim 7 is objected to but otherwise allowable.
Claims 5 and 10-14 are rejected.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to PHILLIP MATTHEW RZECZYCKI whose telephone number is (703)756-5326. The examiner can normally be reached Monday Thru Friday 730AM-5PM EST.
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/P.M.R./Examiner, Art Unit 1625
/JOHN S KENYON/Primary Patent Examiner, Art Unit 1625
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